AS004

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Solvent Coefficients For Sustainable Solvents

Researchers: Jean-Claude Bradley, William E Acree Jr., and Andrew SID Lang
All content, models and data are released as CC0 - the default license for all our ONS work.
This page is a duplicate (backup) of the original ONSChallenge page AbrahamSolventModel004

Objective

To investigate the predicted solvation properties of a comprehensive list of sustainable solvents.[1] These solvents will be compared to solvents with known Abraham solvent coefficients with the outlook of both potentially replacing existing solvents with safer sustainable solvents and to find potential new safe solvents whose solvation properties can then be approximated through their predicted solvent coefficients.

Background

The Abraham general solvation model uses the LFER

log P = c + e E + s S + a A + b B + v V

where c,e,s,a,b,v are the solvent coefficients and E,S,A,B,V are the solute descriptors, see this brief discussion of the model. The Abraham coefficients are found via linear regression from measured data. The standard procedure is to allow the c-coefficient (the intercept) to float in the linear regression. It has been suggested that c should not be negative.[2] We suggest that little predictive ability will be lost if we just require c to be zero. This will also allow easier comparison between solvents. Thus in order to compare both current solvents with each other and potential new solvents with current solvents, we decided to re-calculate the coefficients for known solvents e_0, s_0, a_0, b_0, v_0 by making c zero, see Solvents Model 003.

Then the models themselves can be applied to new compounds to get predicted solvent coefficients which in turn can be used to predict log P for compounds with known Abraham descriptors using the following equation:

log P = e_0 E + s_0 S + a_0 A + b_0 B + v_0 V

Procedure

The supplementary data from the paper by Moity et. al. consists of two files containing lists of solvents with names and CAS numbers. The first file of classical organic solvents was downloaded and ChemSpider IDs (CSIDs) and structures (SMILES) were added by cross-referencing the names and CAS numbers on ChemSpider. The second file of green solvents was downloaded and ChemSpider IDs and structures (SMILES) were added by cross-referencing the names and CAS numbers on ChemSpider. There was one row (menthanyl acetate) that listed a CAS for a similar but different compound (menthyl acetate). Both compounds were kept. CDK descriptors were calculated for all solvents using Rajarshi Guha's CDK DESCUI (v 1.4.2). The option to "Add explicit H" was selected and the descriptors were output as csv files (comma delimited). These files were then loaded into R (R i386 3.0.0) to calculate the predicted solvation coefficients using the following code:
library("randomForest") #for modeling (randomForest 4.6-7)
setwd(".../SustainableSolvents")
myclassicdata = read.csv(file="classicdescriptors.csv",head=TRUE,row.names="Title")
mygreendata = read.csv(file="greendescriptors.csv",head=TRUE,row.names="Title")
 
## load the model for the 'e' coefficient
mydata.rf <- readRDS("erfmodel")
 
## predict using the random forest model
test.predict <- predict(mydata.rf,myclassicdata)
## write the predictions to the working directory
write.csv(test.predict, file = "RFTestPredictClassice.csv")
 
## predict using the random forest model
test.predict <- predict(mydata.rf,mygreendata)
## write the predictions to the working directory
write.csv(test.predict, file = "RFTestPredictGreene.csv")
 
## Similarly for the other coefficients s,a,b, and v
mydata.rf <- readRDS("srfmodel")
test.predict <- predict(mydata.rf,myclassicdata)
write.csv(test.predict, file = "RFTestPredictClassics.csv")
test.predict <- predict(mydata.rf,mygreendata)
write.csv(test.predict, file = "RFTestPredictGreens.csv")
 
mydata.rf <- readRDS("arfmodel")
test.predict <- predict(mydata.rf,myclassicdata)
write.csv(test.predict, file = "RFTestPredictClassica.csv")
test.predict <- predict(mydata.rf,mygreendata)
write.csv(test.predict, file = "RFTestPredictGreena.csv")
 
mydata.rf <- readRDS("brfmodel")
test.predict <- predict(mydata.rf,myclassicdata)
write.csv(test.predict, file = "RFTestPredictClassicb.csv")
test.predict <- predict(mydata.rf,mygreendata)
write.csv(test.predict, file = "RFTestPredictGreenb.csv")
 
mydata.rf <- readRDS("vrfmodel")
test.predict <- predict(mydata.rf,myclassicdata)
write.csv(test.predict, file = "RFTestPredictClassicv.csv")
test.predict <- predict(mydata.rf,mygreendata)
write.csv(test.predict, file = "RFTestPredictGreenv.csv")

Results

The results are listed in the tables below.

Solvents With Known Coefficients

Note the new (updated) coefficients for tributyl phosphate (as compared to the values listed in model003).
c
 e
 s
 a
 b
 v
 solvent
 e_0
 s_0
 a_0
 b_0
 v_0
0.17
 0.4
 -1.01
 0.06
 -3.96
 4.04
 1-butanol
 0.387596
 -0.97209
 0.108258
 -3.97885
 4.12895
0.22
 0.27
 -0.57
 -2.92
 -4.88
 4.46
 1-chlorobutane
 0.254833
 -0.516892
 -2.847674
 -4.910816
 4.57048
-0.06
 0.62
 -1.32
 0.03
 -4.15
 4.28
 1-decanol
 0.6203042
 -1.3327395
 0.0090799
 -4.1464701
 4.2497972
0.04
 0.4
 -1.06
 0
 -4.34
 4.32
 1-heptanol
 0.3948325
 -1.0545913
 0.0143256
 -4.3468223
 4.3352649
0.12
 0.71
 -1.62
 -3.18
 -4.8
 4.32
 1-hexadecene
 0.696611
 -1.588924
 -3.143734
 -4.810655
 4.38202
0.12
 0.49
 -1.16
 0.05
 -3.98
 4.13
 1-hexanol
 0.482763
 -1.137261
 0.090893
 -3.993082
 4.190662
-0.03
 0.49
 -1.04
 -0.02
 -4.24
 4.22
 1-octanol
 0.4909845
 -1.0517092
 -0.0336817
 -4.2309735
 4.2009611
0.15
 0.54
 -1.23
 0.14
 -3.86
 4.08
 1-pentanol
 0.52385
 -1.193867
 0.188379
 -3.88273
 4.154244
0.14
 0.41
 -1.03
 0.25
 -3.77
 3.99
 1-propanol
 0.393466
 -0.996062
 0.291203
 -3.784515
 4.05757
0.18
 0.29
 -0.13
 -2.8
 -4.29
 4.18
 1,2-dichloroethane
 0.278894
 -0.090721
 -2.742532
 -4.313978
 4.274203
0.12
 0.35
 -0.03
 -0.58
 -4.81
 4.11
 1,4-dioxane
 0.33675
 -0.003994
 -0.542209
 -4.825876
 4.173499
0.1
 0.62
 -1.8
 -3.07
 -4.29
 4.52
 1,9-decadiene
 0.606347
 -1.771424
 -3.037034
 -4.304097
 4.571908
0.13
 0.25
 -0.98
 0.16
 -3.88
 4.11
 2-butanol
 0.242337
 -0.945988
 0.198721
 -3.897972
 4.179391
0.19
 0.35
 -1.13
 0.02
 -3.57
 3.97
 2-methyl-1-propanol
 0.338508
 -1.082867
 0.07594
 -3.591543
 4.064762
0.21
 0.17
 -0.95
 0.33
 -4.09
 4.11
 2-methyl-2-propanol
 0.153709
 -0.897144
 0.397899
 -4.111567
 4.217508
0.12
 0.46
 -1.33
 0.21
 -3.75
 4.2
 2-pentanol
 0.445389
 -1.303994
 0.243289
 -3.759434
 4.260301
0.1
 0.34
 -1.05
 0.41
 -3.83
 4.03
 2-propanol
 0.334933
 -1.025916
 0.437909
 -3.839249
 4.084005
0.32
 0.51
 -1.69
 -3.69
 -4.81
 4.4
 2,2,4-trimethylpentane
 0.485433
 -1.610035
 -3.586041
 -4.850718
 4.563507
0.07
 0.36
 -1.27
 0.09
 -3.77
 4.4
 3-methyl-1-butanol
 0.35352
 -1.255543
 0.11342
 -3.779382
 4.43679
0.31
 0.31
 -0.12
 -0.61
 -4.75
 3.94
 acetone
 0.286706
 -0.04747
 -0.508846
 -4.792269
 4.102844
0.41
 0.08
 0.33
 -1.57
 -4.39
 3.36
 acetonitrile
 0.044129
 0.423135
 -1.4362
 -4.443325
 3.576285
0.14
 0.46
 -0.59
 -3.01
 -4.63
 4.49
 benzene
 0.452175
 -0.554143
 -2.963555
 -4.643338
 4.564318
0.1
 0.29
 0.06
 -1.61
 -4.56
 4.03
 benzonitrile
 0.277045
 0.081936
 -1.574291
 -4.574904
 4.07839
-0.02
 0.44
 -0.42
 -3.17
 -4.56
 4.45
 bromobenzene
 0.4369346
 -0.4279276
 -3.1781219
 -4.5563083
 4.4367652
0.25
 0.26
 -0.08
 -0.77
 -4.86
 4.15
 butanone
 0.236179
 -0.022077
 -0.68909
 -4.886268
 4.274532
0.25
 0.36
 -0.5
 -0.87
 -4.97
 4.28
 butyl acetate
 0.336024
 -0.442788
 -0.788152
 -5.004535
 4.408761
0.05
 0.69
 -0.94
 -3.6
 -5.82
 4.92
 carbon disulfide
 0.6819348
 -0.9318396
 -3.5870443
 -5.8248542
 4.9458403
0.2
 0.52
 -1.16
 -3.56
 -4.59
 4.62
 carbon tetrachloride
 0.506806
 -1.112282
 -3.496545
 -4.619008
 4.720644
0.07
 0.38
 -0.52
 -3.18
 -4.7
 4.61
 chlorobenzene
 0.3752336
 -0.5056045
 -3.1613969
 -4.7083071
 4.6478423
0.19
 0.11
 -0.4
 -3.11
 -3.51
 4.4
 chloroform
 0.089413
 -0.357874
 -3.051291
 -3.537934
 4.493193
0.16
 0.78
 -1.68
 -3.74
 -4.93
 4.58
 cyclohexane
 0.770769
 -1.640414
 -3.689346
 -4.948869
 4.659072
0.04
 0.23
 0.06
 -0.98
 -4.84
 4.32
 cyclohexanone
 0.2216766
 0.0668337
 -0.962833
 -4.8469389
 4.3348761
0.19
 0.72
 -1.74
 -3.45
 -4.97
 4.48
 decane
 0.706653
 -1.697274
 -3.389851
 -4.993254
 4.571974
0.18
 0.39
 -0.99
 -1.41
 -5.36
 4.52
 dibutyl ether
 0.37973
 -0.94367
 -1.357836
 -5.379393
 4.614845
0.33
 0.3
 -0.44
 0.36
 -4.9
 3.95
 dibutylformamide
 0.275223
 -0.3577
 0.462459
 -4.944045
 4.122737
0.32
 0.1
 -0.19
 -3.06
 -4.09
 4.32
 dichloromethane
 0.076325
 -0.111839
 -2.957248
 -4.130085
 4.487963
0.35
 0.36
 -0.82
 -0.59
 -4.96
 4.35
 diethyl ether
 0.329941
 -0.737491
 -0.477868
 -5.000297
 4.530001
0.21
 0.03
 0.09
 1.34
 -5.08
 4.09
 diethylacetamide
 0.0167
 0.139253
 1.409338
 -5.111165
 4.197615
-0.27
 0.08
 0.21
 0.92
 -5
 4.56
 dimethylacetamide
 0.104844
 0.145499
 0.831639
 -4.970213
 4.418588
-0.31
 -0.06
 0.34
 0.36
 -4.87
 4.49
 DMF
 -0.034208
 0.27126
 0.264139
 -4.827615
 4.330082
-0.19
 0.33
 0.79
 1.26
 -4.54
 3.36
 DMSO
 0.341749
 0.745718
 1.200253
 -4.516908
 3.262081
0.11
 0.67
 -1.64
 -3.55
 -5.01
 4.46
 dodecane
 0.658583
 -1.616828
 -3.508611
 -5.020509
 4.517868
0.22
 0.47
 -1.04
 0.33
 -3.6
 3.86
 ethanol
 0.453079
 -0.983328
 0.396198
 -3.623493
 3.971272
-0.17
 -0.02
 0
 0.07
 -0.37
 0.45
 ethanol/water(10:90)vol
 -0.009316
 -0.04156
 0.010626
 -0.350331
 0.365271
-0.25
 0.04
 -0.04
 0.1
 -0.83
 0.92
 ethanol/water(20:80)vol
 0.062777
 -0.098993
 0.01722
 -0.800521
 0.786631
-0.27
 0.11
 -0.1
 0.13
 -1.32
 1.41
 ethanol/water(30:70)vol
 0.127804
 -0.160996
 0.049426
 -1.282852
 1.276293
-0.22
 0.13
 -0.16
 0.17
 -1.81
 1.92
 ethanol/water(40:60)vol
 0.148332
 -0.210817
 0.102648
 -1.781936
 1.804907
-0.14
 0.12
 -0.25
 0.25
 -2.28
 2.42
 ethanol/water(50:50)vol
 0.134901
 -0.285203
 0.207128
 -2.257463
 2.342294
-0.04
 0.14
 -0.34
 0.29
 -2.68
 2.81
 ethanol/water(60:40)vol
 0.1406465
 -0.3442878
 0.281256
 -2.6697239
 2.7916452
0.06
 0.09
 -0.37
 0.31
 -2.94
 3.1
 ethanol/water(70:30)vol
 0.0794107
 -0.3529953
 0.331463
 -2.9438845
 3.1344568
0.17
 0.18
 -0.47
 0.26
 -3.21
 3.32
 ethanol/water(80:20)vol
 0.161026
 -0.424495
 0.314211
 -3.233463
 3.411426
0.24
 0.21
 -0.58
 0.26
 -3.45
 3.55
 ethanol/water(90:10)vol
 0.193477
 -0.51767
 0.338521
 -3.480739
 3.669878
0.33
 0.37
 -0.45
 -0.7
 -4.9
 4.15
 ethyl acetate
 0.342809
 -0.369036
 -0.596948
 -4.94523
 4.318697
0.09
 0.47
 -0.72
 -3
 -4.84
 4.51
 ethylbenzene
 0.459437
 -0.701228
 -2.970828
 -4.855741
 4.56218
-0.27
 0.58
 -0.51
 0.72
 -2.62
 2.73
 ethylene glycol
 0.599449
 -0.574819
 0.631321
 -2.585314
 2.5908
0.14
 0.15
 -0.37
 -3.03
 -4.6
 4.54
 fluorobenzene
 0.140337
 -0.340978
 -2.985464
 -4.618238
 4.611483
-0.17
 0.07
 0.31
 0.59
 -3.15
 2.43
 formamide
 0.083307
 0.267828
 0.536608
 -3.131516
 2.344771
0.3
 0.64
 -1.76
 -3.57
 -4.95
 4.49
 heptane
 0.61919
 -1.685129
 -3.477189
 -4.983132
 4.640776
0.09
 0.67
 -1.62
 -3.59
 -4.87
 4.43
 hexadecane
 0.659893
 -1.59632
 -3.559573
 -4.880281
 4.47815
0.33
 0.56
 -1.71
 -3.58
 -4.94
 4.46
 hexane
 0.53342
 -1.631725
 -3.473425
 -4.980698
 4.634317
-0.19
 0.3
 -0.31
 -3.21
 -4.65
 4.59
 iodobenzene
 0.312539
 -0.352762
 -3.271785
 -4.629052
 4.489752
-0.61
 0.93
 -1.15
 -1.68
 -4.09
 4.25
 isopropyl myristate
 0.977259
 -1.294959
 -1.870114
 -4.017729
 3.939081
0.12
 0.38
 -0.6
 -2.98
 -4.96
 4.54
 m-xylene
 0.366587
 -0.574078
 -2.941283
 -4.976929
 4.598299
0.28
 0.33
 -0.71
 0.24
 -3.32
 3.55
 methanol
 0.311909
 -0.649107
 0.329542
 -3.354582
 3.690751
0.35
 0.22
 -0.15
 -1.04
 -4.53
 3.97
 methyl acetate
 0.194997
 -0.067588
 -0.923983
 -4.571216
 4.15239
0.34
 0.31
 -0.82
 -0.62
 -5.1
 4.43
 methyl tert-butyl ether
 0.279699
 -0.737134
 -0.510026
 -5.139775
 4.600429
0.25
 0.78
 -1.98
 -3.52
 -4.29
 4.53
 methylcyclohexane
 0.762327
 -1.924196
 -3.439318
 -4.323834
 4.654703
0.28
 0.13
 -0.44
 1.18
 -4.73
 3.86
 N-ethylacetamide
 0.105071
 -0.374993
 1.269385
 -4.764184
 4.002187
0.22
 0.03
 -0.17
 0.94
 -4.59
 3.73
 N-ethylformamide
 0.016449
 -0.114321
 1.004651
 -4.616979
 3.84333
-0.03
 0.7
 -0.06
 0.01
 -4.09
 3.41
 N-formylmorpholine
 0.6981457
 -0.0694897
 0.0048883
 -4.0885654
 3.38906
0.06
 0.33
 0.26
 1.56
 -5.04
 3.98
 N-methyl-2-piperidone
 0.3271873
 0.2705115
 1.5746338
 -5.0436057
 4.0124292
0.09
 0.21
 -0.17
 1.31
 -4.59
 3.83
 N-methylacetamide
 0.19721
 -0.150831
 1.334533
 -4.600626
 3.879615
0.11
 0.41
 -0.29
 0.54
 -4.09
 3.47
 N-methylformamide
 0.397604
 -0.260136
 0.578616
 -4.099689
 3.529845
0.15
 0.53
 0.23
 0.84
 -4.79
 3.67
 N-methylpyrrolidinone
 0.519565
 0.259902
 0.887089
 -4.813222
 3.749914
-0.2
 0.54
 0.04
 -2.33
 -4.61
 4.31
 nitrobenzene
 0.551741
 -0.003723
 -2.388352
 -4.584066
 4.213974
0.02
 -0.09
 0.79
 -1.46
 -4.36
 3.46
 nitromethane
 -0.0933342
 0.7985957
 -1.4544755
 -4.3676129
 3.4722537
0.24
 0.62
 -1.71
 -3.53
 -4.92
 4.48
 nonane
 0.599859
 -1.65665
 -3.456521
 -4.951366
 4.605711
0.08
 0.52
 -0.81
 -2.88
 -4.82
 4.56
 o-xylene
 0.511059
 -0.793315
 -2.857401
 -4.831364
 4.601817
-0.1
 0.15
 -0.84
 -0.44
 -4.04
 4.13
 octadecanol
 0.155261
 -0.863525
 -0.466854
 -4.028093
 4.075935
0.23
 0.74
 -1.84
 -3.59
 -4.91
 4.5
 octane
 0.719433
 -1.785636
 -3.512058
 -4.936095
 4.620999
0.17
 0.48
 -0.81
 -2.94
 -4.87
 4.53
 p-xylene
 0.463092
 -0.772761
 -2.885801
 -4.895116
 4.617725
0.37
 0.39
 -1.57
 -3.54
 -5.22
 4.51
 pentane
 0.35651
 -1.481294
 -3.418818
 -5.261024
 4.703599
0
 0.17
 0.5
 -1.28
 -4.41
 3.42
 propylene carbonate
 0.1672359
 0.505135
 -1.2809844
 -4.4080414
 3.4234811
0
 0.15
 0.6
 -0.38
 -4.54
 3.29
 sulfolane
 0.1468503
 0.6009136
 -0.3799049
 -4.541574
 3.2903215
0.22
 0.36
 -0.38
 -0.24
 -4.93
 4.45
 THF
 0.345051
 -0.331628
 -0.167145
 -4.96046
 4.564853
0.13
 0.43
 -0.64
 -3
 -4.75
 4.52
 toluene
 0.420597
 -0.614527
 -2.961869
 -4.763681
 4.588524
0.02
 0.35
 -0.43
 0.71
 -4.73
 4.19
 tributyl phosphate
 0.3482619
 -0.4268337
 0.7148701
 -4.7277409
 4.2032817
0.4
 -0.09
 -0.59
 -1.28
 -1.27
 3.09
 trifluoroethanol
 -0.125647
 -0.50143
 -1.155862
 -1.322677
 3.290636
0.06
 0.6
 -1.66
 -3.42
 -5.12
 4.62
 undecane
 0.5979334
 -1.6471654
 -3.4017847
 -5.1276719
 4.6493317

Predicted Coefficients e_0, s_0, a_0, b_0, and v_0 for classic solvents

solvent
 CAS
 CSID
 SMILES
 e_0
 s_0
 a_0
 b_0
 v_0
n-butylamine
 109-73-9
 7716
 CCCCN
 0.401
 -0.861
 -0.757
 -4.572
 4.266
diethylamine
 109-89-7
 7730
 CCNCC
 0.277
 -0.653
 -0.77
 -4.684
 4.431
n-propylamine
 107-10-8
 7564
 CCCN
 0.394
 -0.809
 -0.664
 -4.412
 4.159
piperidine
 110-89-4
 7791
 C1CCNCC1
 0.413
 -0.703
 -0.934
 -4.664
 4.434
pyrrolidine
 123-75-1
 29008
 C1CCNC1
 0.375
 -0.555
 -0.812
 -4.653
 4.387
tributylamine
 102-82-9
 7340
 CCCCN(CCCC)CCCC
 0.535
 -1.086
 -1.635
 -4.942
 4.432
triethylamine
 121-44-8
 8158
 CCN(CC)CC
 0.367
 -0.545
 -1.349
 -4.943
 4.504
tert-butyl methyl ether
 1634-04-4
 14672
 CC(C)(C)OC
 0.285
 -0.71
 -0.534
 -4.898
 4.498
acetone
 67-64-1
 175
 CC(=O)C
 0.252
 -0.063
 -0.389
 -4.721
 4.092
DMEU
 80-73-9
 6409
 CN1CCN(C1=O)C
 0.315
 0.175
 0.319
 -4.7
 3.702
DPMU
 7226-23-5
 73671
 CN1CCCN(C1=O)C
 0.355
 0.119
 0.259
 -4.748
 3.85
N,N-dimethylacetamide
 127-19-5
 29107
 CC(=O)N(C)C
 0.173
 0.071
 0.579
 -4.781
 4.079
N,N-dimethylformamide
 68-12-2
 5993
 CN(C)C=O
 0.187
 0.014
 0.111
 -4.521
 3.827
2,4-dimethylpyridine
 108-47-4
 21132380
 CC1=CC(=NC=C1)C
 0.312
 -0.364
 -0.716
 -4.846
 4.417
2,6-dimethylpyridine
 108-48-5
 13842613
 CC1=NC(=CC=C1)C
 0.328
 -0.344
 -0.811
 -4.865
 4.407
ethylenediamine
 107-15-3
 13835550
 C(CN)N
 0.439
 -0.604
 -0.369
 -4.133
 3.538
HMPTA
 680-31-9
 12158
 CN(C)P(=O)(N(C)C)N(C)C
 0.289
 0.052
 0.2
 -4.41
 3.645
N-methyl-pyrrolidin-2-one
 872-50-4
 12814
 CN1CCCC1=O
 0.408
 0.195
 0.217
 -4.68
 3.827
morpholine
 110-91-8
 13837537
 C1COCCN1
 0.324
 -0.346
 0.053
 -4.308
 3.938
3-picoline
 108-99-6
 21106520
 CC1=CN=CC=C1
 0.299
 -0.317
 -0.625
 -4.724
 4.418
4-picoline
 108-89-4
 13874733
 CC1=CC=NC=C1
 0.314
 -0.35
 -0.641
 -4.716
 4.46
pyridine
 110-86-1
 1020
 C1=CC=NC=C1
 0.316
 -0.35
 -0.65
 -4.682
 4.399
quinoline
 91-22-5
 6780
 C1=CC=C2C(=C1)C=CC=N2
 0.391
 -0.343
 -1.184
 -4.643
 4.38
tetrahydrofuran
 109-99-9
 7737
 C1CCOC1
 0.344
 -0.346
 -0.369
 -4.87
 4.465
1,1,3,3-tetramethyl urea
 632-22-4
 11930
 CN(C)C(=O)N(C)C
 0.193
 0.118
 0.34
 -4.732
 3.914
2,4,6-trimethylpyridine
 108-75-8
 21106174
 CC1=CC(=NC(=C1)C)C
 0.331
 -0.427
 -0.931
 -4.827
 4.374
triethylene glycol
 112-27-6
 13835895
 C(COCCOCCO)O
 0.497
 -0.416
 -0.149
 -3.292
 3.484
1-chlorobutane
 109-69-3
 7714
 CCCCCl
 0.315
 -0.642
 -2.847
 -4.684
 4.534
acetophenone
 98-86-2
 7132
 CC(=O)C1=CC=CC=C1
 0.343
 -0.199
 -0.751
 -4.753
 4.179
benzaldehyde
 100-52-7
 235
 C1=CC=C(C=C1)C=O
 0.323
 -0.183
 -0.802
 -4.569
 4.152
2-butanone
 78-93-3
 6321
 CCC(=O)C
 0.229
 -0.128
 -0.536
 -4.814
 4.208
n-butyl acetate
 123-86-4
 29012
 CCCCOC(=O)C
 0.321
 -0.434
 -0.803
 -4.887
 4.298
di-n-butyl ether
 142-96-1
 8569
 CCCCOCCCC
 0.396
 -0.874
 -1.009
 -5.155
 4.548
butyronitrile
 109-74-0
 7717
 CCCC#N
 0.247
 -0.296
 -1.057
 -4.556
 4.137
cyclohexanone
 108-94-1
 7679
 C1CCC(=O)CC1
 0.279
 -0.004
 -0.793
 -4.779
 4.227
cyclopentanone
 120-92-3
 8141
 C1CCC(=O)C1
 0.298
 0.031
 -0.563
 -4.765
 4.164
DEGDEE
 112-36-7
 21106583
 CCOCCOCCOCC
 0.367
 -0.377
 -0.574
 -4.503
 4.043
DEGDME
 111-96-6
 13839575
 COCCOCCOC
 0.38
 -0.514
 -0.417
 -4.324
 3.922
dibenzyl ether
 103-50-4
 21105876
 C1=CC=C(C=C1)COCC2=CC=CC=C2
 0.472
 -0.698
 -0.972
 -4.701
 4.333
diethyl carbonate
 105-58-8
 7478
 CCOC(=O)OCC
 0.318
 -0.262
 -0.968
 -4.629
 4.063
diethyl ether
 60-29-7
 3168
 CCOCC
 0.314
 -0.625
 -0.517
 -4.932
 4.464
di-isopropyl ether
 108-20-3
 7626
 CC(C)OC(C)C
 0.284
 -0.472
 -0.639
 -4.838
 4.488
1,2-dimethoxyethane
 110-71-4
 13836589
 COCCOC
 0.36
 -0.547
 -0.379
 -4.524
 4.038
3,3-dimethyl-2-butanone
 75-97-8
 6176
 CC(=O)C(C)(C)C
 0.25
 -0.262
 -0.574
 -4.877
 4.237
2,6-dimethyl-4-heptanone
 108-83-8
 7670
 CC(C)CC(=O)CC(C)C
 0.346
 -0.593
 -0.718
 -4.826
 4.247
2,4-dimethyl-3-pentanone
 565-80-0
 10797
 CC(C)C(=O)C(C)C
 0.281
 -0.375
 -0.547
 -4.822
 4.279
1,4-dioxane
 123-91-1
 29015
 C1COCCO1
 0.345
 -0.189
 -0.416
 -4.497
 4.084
ethyl acetate
 141-78-6
 8525
 CCOC(=O)C
 0.262
 -0.298
 -0.7
 -4.868
 4.252
ethyl benzoate
 93-89-0
 6897
 CCOC(=O)C1=CC=CC=C1
 0.366
 -0.297
 -1.161
 -4.65
 4.127
ethyl formate
 109-94-4
 7734
 CCOC=O
 0.227
 -0.116
 -0.805
 -4.483
 3.778
ethyl propionate
 105-37-3
 7463
 CCC(=O)OCC
 0.249
 -0.284
 -0.646
 -4.873
 4.236
methyl acetate
 79-20-9
 6335
 CC(=O)OC
 0.217
 -0.055
 -0.657
 -4.563
 3.919
methyl benzoate
 93-58-3
 6883
 COC(=O)C1=CC=CC=C1
 0.36
 -0.225
 -1.149
 -4.63
 4.109
3-methyl-2-butanone
 563-80-4
 10777
 CC(C)C(=O)C
 0.22
 -0.159
 -0.405
 -4.826
 4.265
4-methyl-2-pentanone
 108-10-1
 7621
 CC(C)CC(=O)C
 0.249
 -0.417
 -0.527
 -4.804
 4.276
2-pentanone
 107-87-9
 7607
 CCCC(=O)C
 0.275
 -0.4
 -0.511
 -4.887
 4.244
3-pentanone
 96-22-0
 7016
 CCC(=O)CC
 0.252
 -0.326
 -0.537
 -4.899
 4.25
pentyl actetae
 628-63-7
 11843
 CCCCCOC(=O)C
 0.378
 -0.5
 -0.818
 -4.832
 4.259
di-n-propyl ether
 111-43-3
 7823
 CCCOCCC
 0.358
 -0.727
 -0.66
 -5.091
 4.54
propyl formate
 110-74-7
 7782
 CCCOC=O
 0.295
 -0.242
 -0.734
 -4.604
 3.939
TEGDME
 143-24-8
 13835433
 COCCOCCOCCOCCOC
 0.407
 -0.552
 -0.505
 -4.105
 3.644
benzonitrile
 100-47-0
 7224
 C1=CC=C(C=C1)C#N
 0.302
 -0.106
 -1.427
 -4.566
 4.159
chloroform
 67-66-3
 5977
 C(Cl)(Cl)Cl
 0.203
 -0.405
 -3.075
 -4.029
 4.504
acetic anhydride
 108-24-7
 7630
 CC(=O)OC(=O)C
 0.219
 -0.008
 -0.604
 -4.652
 4.007
acetonitrile
 75-05-8
 6102
 CC#N
 0.119
 0.132
 -1.151
 -4.25
 3.656
acetylacetone
 123-54-6
 29001
 CC(=O)CC(=O)C
 0.233
 -0.057
 -0.279
 -4.703
 4.029
dimethylsulfoxide
 67-68-5
 659
 CS(=O)C
 0.304
 0.375
 0.599
 -4.534
 3.542
N-methylacetamide
 79-16-3
 6334
 CC(=O)NC
 0.139
 0.021
 0.605
 -4.574
 4.031
N-methylformamide
 123-39-7
 28994
 CNC=O
 0.245
 -0.096
 0.323
 -4.182
 3.527
methyl formate
 107-31-3
 7577
 COC=O
 0.216
 0.015
 -0.647
 -4.146
 3.569
propionitrile
 107-12-0
 7566
 CCC#N
 0.233
 -0.144
 -1.049
 -4.459
 3.949
propylene carbonate
 108-32-7
 7636
 CC1COC(=O)O1
 0.223
 0.302
 -1.03
 -4.388
 3.577
sulfolane
 126-33-0
 29080
 C1CCS(=O)(=O)C1
 0.238
 0.398
 -0.405
 -4.607
 3.567
2-butanol
 78-92-2
 6320
 CCC(C)O
 0.294
 -0.972
 0.186
 -3.85
 4.155
benzene
 71-43-2
 236
 C1=CC=CC=C1
 0.445
 -0.612
 -3.109
 -4.697
 4.565
bromobenzene
 108-86-1
 7673
 C1=CC=C(C=C1)Br
 0.42
 -0.506
 -3.167
 -4.581
 4.499
1-bromobutane
 109-65-9
 7711
 CCCCBr
 0.34
 -0.688
 -2.993
 -4.626
 4.549
bromoethane
 74-96-4
 6092
 CCBr
 0.361
 -0.614
 -2.995
 -4.606
 4.569
carbon disulfide
 75-15-0
 6108
 C(=S)=S
 0.485
 -0.683
 -3.02
 -5.194
 4.628
carbon tetrachloride
 56-23-5
 5730
 C(Cl)(Cl)(Cl)Cl
 0.404
 -0.782
 -3.224
 -4.305
 4.558
chlorobenzene
 108-90-7
 7676
 C1=CC=C(C=C1)Cl
 0.385
 -0.483
 -3.087
 -4.617
 4.575
3-methyl-1-butanol
 123-51-3
 29000
 CC(C)CCO
 0.349
 -1.101
 0.102
 -3.833
 4.283
1-chloropropane
 540-54-5
 10437
 CCCCl
 0.324
 -0.623
 -2.795
 -4.649
 4.536
2-chloropropane
 75-29-6
 6121
 CC(C)Cl
 0.327
 -0.674
 -2.939
 -4.559
 4.552
cis-decaline
 91-17-8
 10179239
 C1C[C@@H]2[C@@H](CCCC2)CC1
 0.643
 -1.529
 -3.488
 -4.689
 4.557
cyclohexane
 110-82-7
 7787
 C1CCCCC1
 0.663
 -1.478
 -3.524
 -4.88
 4.653
cyclohexene
 110-83-8
 7788
 C1CCC=CC1
 0.475
 -0.893
 -3.132
 -4.741
 4.642
cyclopentane
 287-92-3
 8896
 C1CCCC1
 0.535
 -1.133
 -3.416
 -4.897
 4.658
n-decane
 124-18-5
 14840
 CCCCCCCCCC
 0.667
 -1.682
 -3.427
 -4.988
 4.592
o-dichlorobenzene
 95-50-1
 13837988
 C1=CC=C(C(=C1)Cl)Cl
 0.412
 -0.539
 -3.075
 -4.593
 4.448
1,1-dichloroethylene
 75-35-4
 13835316
 C=C(Cl)Cl
 0.346
 -0.554
 -3.143
 -4.492
 4.55
m-dichlorobenzene
 541-73-1
 13857694
 C1=CC(=CC(=C1)Cl)Cl
 0.391
 -0.581
 -3.061
 -4.588
 4.459
N,N-dimethylaniline
 121-69-7
 924
 CN(C)C1=CC=CC=C1
 0.39
 -0.437
 -1.318
 -4.757
 4.433
diphenyl ether
 101-84-8
 7302
 C1=CC=C(C=C1)OC2=CC=CC=C2
 0.418
 -0.644
 -1.778
 -4.664
 4.372
fluorobenzene
 462-06-6
 9614
 C1=CC=C(C=C1)F
 0.288
 -0.372
 -2.385
 -4.599
 4.506
n-heptane
 142-82-5
 8560
 CCCCCCC
 0.609
 -1.673
 -3.457
 -4.98
 4.633
n-hexane
 110-54-3
 7767
 CCCCCC
 0.539
 -1.618
 -3.423
 -5.001
 4.643
iodobenzene
 591-50-4
 11087
 C1=CC=C(C=C1)I
 0.406
 -0.659
 -3.217
 -4.572
 4.509
iodoethane
 75-03-6
 6100
 CCI
 0.433
 -0.727
 -3.147
 -4.685
 4.582
mesitylene
 108-67-8
 7659
 CC1=CC(=CC(=C1)C)C
 0.494
 -1.032
 -3.149
 -4.91
 4.567
iso-octane
 540-84-1
 10445
 CC(C)CC(C)(C)C
 0.509
 -1.53
 -3.446
 -4.837
 4.585
n-octane
 111-65-9
 349
 CCCCCCCC
 0.666
 -1.708
 -3.474
 -4.961
 4.621
n-pentane
 109-66-0
 7712
 CCCCC
 0.412
 -1.414
 -3.316
 -5.057
 4.639
phenetole
 103-73-1
 7391
 CCOC1=CC=CC=C1
 0.354
 -0.424
 -1.636
 -4.8
 4.491
styrene
 100-42-5
 7220
 C=CC1=CC=CC=C1
 0.472
 -0.732
 -3.147
 -4.73
 4.57
tetrachloroethylene
 127-18-4
 13837281
 C(=C(Cl)Cl)(Cl)Cl
 0.354
 -0.482
 -3.045
 -4.235
 4.348
toluene
 108-88-3
 1108
 CC1=CC=CC=C1
 0.429
 -0.609
 -2.979
 -4.751
 4.588
1,1,1-trichloroethane
 71-55-6
 6042
 CC(Cl)(Cl)Cl
 0.321
 -0.636
 -3.192
 -4.384
 4.549
trichloroethylene
 79-01-6
 13837280
 C(=C(Cl)Cl)Cl
 0.292
 -0.344
 -2.959
 -4.395
 4.347
m-xylene
 108-38-3
 7641
 CC1=CC(=CC=C1)C
 0.408
 -0.689
 -2.945
 -4.919
 4.594
o-xylene
 95-47-6
 6967
 CC1=CC=CC=C1C
 0.473
 -0.747
 -2.932
 -4.867
 4.595
p-xylene
 106-42-3
 7521
 CC1=CC=C(C=C1)C
 0.455
 -0.747
 -2.907
 -4.89
 4.597
aniline
 62-53-3
 5889
 C1=CC=C(C=C1)N
 0.351
 -0.461
 -1.055
 -4.481
 4.324
anisole
 100-66-3
 7238
 COC1=CC=CC=C1
 0.356
 -0.344
 -1.516
 -4.723
 4.501
1,1-dichloroethane
 75-34-3
 6125
 CC(Cl)Cl
 0.282
 -0.416
 -2.988
 -4.365
 4.497
1,2-dichloroethane
 107-06-2
 13837650
 C(CCl)Cl
 0.299
 -0.206
 -2.757
 -4.439
 4.352
Z-1,2-dichloroethylene
 156-59-2
 558928
 C(=C\\Cl)\\Cl
 0.327
 -0.387
 -2.884
 -4.475
 4.465
dichloromethane
 75-09-2
 6104
 C(Cl)Cl
 0.159
 -0.261
 -2.882
 -4.372
 4.516
nitrobenzene
 98-95-3
 7138
 C1=CC=C(C=C1)[N+](=O)[O-]
 0.443
 -0.119
 -1.974
 -4.527
 4.176
nitroethane
 79-24-3
 6338
 CC[N+](=O)[O-]
 0.243
 -0.192
 -1.409
 -4.449
 3.797
nitromethane
 75-52-5
 6135
 C[N+](=O)[O-]
 0.103
 0.228
 -1.477
 -4.079
 3.534
1,1,2,2-tetrachloroethane
 79-34-5
 6342
 C(C(Cl)Cl)(Cl)Cl
 0.328
 -0.504
 -3.026
 -4.058
 4.325
1-butanol
 71-36-3
 258
 CCCCO
 0.396
 -0.986
 0.145
 -3.914
 4.127
benzyl alcohol
 100-51-6
 13860335
 C1=CC=C(C=C1)CO
 0.365
 -0.399
 -0.381
 -3.949
 4.143
tert-butyl alcohol
 75-65-0
 6146
 CC(C)(C)O
 0.27
 -0.889
 0.228
 -3.979
 4.197
cyclohexanol
 108-93-0
 7678
 C1CCC(CC1)O
 0.369
 -0.726
 -0.267
 -4.035
 4.224
ethanol
 64-17-5
 682
 CCO
 0.378
 -0.906
 0.337
 -3.574
 3.819
1-hexanol
 111-27-3
 7812
 CCCCCCO
 0.446
 -1.065
 0.069
 -3.98
 4.199
isobutyl alcohol
 78-83-1
 6312
 CC(C)CO
 0.327
 -0.997
 0.125
 -3.734
 4.121
2-methyl-2-butanol
 75-85-4
 6165
 CCC(C)(C)O
 0.285
 -0.925
 0.042
 -3.941
 4.29
tetraethylene glycol
 112-60-7
 7908
 C(COCCOCCOCCO)O
 0.49
 -0.423
 -0.31
 -3.297
 3.495
1-pentanol
 71-41-0
 6040
 CCCCCO
 0.448
 -1.071
 0.13
 -3.919
 4.162
2-pentanol
 6032-29-7
 21011
 CCCC(C)O
 0.399
 -1.147
 0.152
 -3.847
 4.22
3-pentanol
 584-02-1
 10947
 CCC(CC)O
 0.355
 -1.044
 0.108
 -3.93
 4.23
1-propanol
 71-23-8
 1004
 CCCO
 0.378
 -0.953
 0.276
 -3.795
 4.038
2-propanol
 67-63-0
 3644
 CC(C)O
 0.332
 -0.956
 0.341
 -3.781
 4.079
1-octanol
 111-87-5
 932
 CCCCCCCCO
 0.461
 -1.066
 -0.057
 -4.141
 4.204
2-aminoethanol
 141-43-5
 13835336
 C(CO)N
 0.432
 -0.5
 0.351
 -3.503
 3.353
ethylene glycol
 107-21-1
 13835235
 C(CO)O
 0.493
 -0.451
 0.375
 -2.968
 2.936
diethylene glycol
 111-46-6
 13835180
 C(COCCO)O
 0.48
 -0.421
 -0.062
 -3.361
 3.478
trimethylene glycol
 504-63-2
 13839553
 C(CO)CO
 0.434
 -0.627
 0.236
 -3.726
 3.6
glycerol
 56-81-5
 733
 C(C(CO)O)O
 0.405
 -0.43
 0.076
 -3.421
 3.476
propylene glycol
 57-55-6
 13835224
 CC(CO)O
 0.387
 -0.447
 0.259
 -3.447
 3.586
methanol
 67-56-1
 864
 CO
 0.286
 -0.631
 0.312
 -3.417
 3.572
2-methoxyethanol
 109-86-4
 7728
 COCCO
 0.385
 -0.472
 0.081
 -3.497
 3.659
furfuryl alcohol
 98-00-0
 7083
 C1=COC(=C1)CO
 0.351
 -0.195
 -0.047
 -3.553
 3.88
acetic acid
 64-19-7
 171
 CC(=O)O
 0.193
 0.016
 -0.103
 -3.625
 3.565
m-cresol
 108-39-4
 21105871
 CC1=CC(=CC=C1)O
 0.377
 -0.591
 -1.325
 -4.069
 4.301
phenol
 108-95-2
 971
 C1=CC=C(C=C1)O
 0.342
 -0.551
 -1.337
 -4.003
 4.324
trifluoroacetic acid
 76-05-1
 10239201
 C(=O)(C(F)(F)F)O
 0.127
 0.009
 -0.675
 -2.89
 3.397
2,2,2-trifluoroethanol
 75-89-8
 21106169
 C(C(F)(F)F)O
 0.032
 -0.46
 -0.768
 -2.499
 3.504
formamide
 75-12-7
 693
 C(=O)N
 0.138
 0.23
 0.437
 -3.584
 2.893
water
 7732-18-5
 937
 O
 0.305
 -0.832
 -1.252
 -3.528
 3.762

Predicted Coefficients e_0, s_0, a_0, b_0, and v_0 for green solvents

solvent
 CAS
 CSID
 SMILES
 e_0
 s_0
 a_0
 b_0
 v_0
Acetone
 67-64-1
 175
 CC(=O)C
 0.252
 -0.063
 -0.389
 -4.721
 4.092
N,N-Dimethyloctanamide
 1118-92-9
 13603
 CCCCCCCC(=O)N(C)C
 0.484
 -0.549
 -0.010
 -4.843
 4.121
Methyl 5-(dimethylamino) 2-methyl-oxopentanoate
 1174627-68-9
 30991450
 CC(CCC(=O)N(C)C)C(=O)OC
 0.323
 -0.119
 -0.405
 -4.378
 3.848
2-Pyrrolidone
 616-45-5
 11530
 C1CC(=O)NC1
 0.306
 0.011
 0.734
 -4.709
 4.020
Methyl palmitate
 112-39-0
 7889
 CCCCCCCCCCCCCCCC(=O)OC
 0.611
 -0.890
 -1.127
 -4.578
 4.076
Acetyl tributyl citrate
 77-90-7
 6259
 CCCCOC(=O)CC(CC(=O)OCCCC)(C(=O)OCCCC)OC(=O)C
 0.689
 -0.837
 -1.091
 -4.415
 3.969
Benzyl benzoate
 120-51-4
 13856959
 C1=CC=C(C=C1)COC(=O)C2=CC=CC=C2
 0.483
 -0.550
 -1.155
 -4.526
 4.072
Butylacetate
 123-86-4
 29012
 CCCCOC(=O)C
 0.321
 -0.434
 -0.803
 -4.887
 4.298
Butyl laurate
 106-18-3
 54975
 CCCCCCCCCCCC(=O)OCCCC
 0.617
 -0.934
 -1.210
 -4.578
 4.108
1,4-Cineol
 470-67-7
 9702
 CC(C)C12CCC(O1)(CC2)C
 0.397
 -0.616
 -0.909
 -4.718
 4.299
1,8-Cineol
 470-82-6
 2656
 CC1(C2CCC(O1)(CC2)C)C
 0.393
 -0.581
 -0.921
 -4.723
 4.316
Cyclopentyl methyl ether
 5614-37-9
 122157
 COC1CCCC1
 0.385
 -0.387
 -0.654
 -4.717
 4.470
Dibutyl sebacate
 109-43-3
 13837584
 CCCCOC(=O)CCCCCCCCC(=O)OCCCC
 0.680
 -0.892
 -1.239
 -4.329
 3.976
Diethyl adipate
 141-28-6
 13835108
 CCOC(=O)CCCCC(=O)OCC
 0.359
 -0.384
 -0.954
 -4.515
 4.025
Diethyl glutarate
 818-38-2
 12610
 CCOC(=O)CCCC(=O)OCC
 0.349
 -0.308
 -0.979
 -4.477
 4.021
Diethyl phthalate
 84-66-2
 13837303
 CCOC(=O)C1=CC=CC=C1C(=O)OCC
 0.444
 -0.397
 -1.082
 -4.412
 4.016
Diethyl succinate
 123-25-1
 13865630
 CCOC(=O)CCC(=O)OCC
 0.354
 -0.169
 -0.897
 -4.480
 3.956
Diisoamylsuccinate
 818-04-2
 63149
 CC(C)CCOC(=O)CCC(=O)OCCC(C)C
 0.571
 -0.700
 -1.006
 -4.286
 3.973
Diisobutyl adipate
 141-04-8
 8499
 CC(C)COC(=O)CCCCC(=O)OCC(C)C
 0.464
 -0.607
 -0.997
 -4.338
 4.007
Diisobutyl glutarate
 71195-64-7
 104603
 CC(C)COC(=O)CCCC(=O)OCC(C)C
 0.481
 -0.543
 -1.019
 -4.301
 4.000
Diisobutyl succinate
 925-06-4
 63400
 CC(C)COC(=O)CCC(=O)OCC(C)C
 0.424
 -0.430
 -1.007
 -4.326
 3.982
Diisooctylsuccinate
 2915-57-3
 92957
 O=C(OCC(CC)CCCC)CCC(=O)OCC(CCCC)CC
 0.711
 -0.861
 -1.127
 -4.262
 3.967
Dimethyl adipate
 627-93-0
 11824
 COC(=O)CCCCC(=O)OC
 0.345
 -0.156
 -0.875
 -4.446
 3.878
Dimethyl glutarate
 1119-40-0
 13605
 COC(=O)CCCC(=O)OC
 0.342
 -0.099
 -0.855
 -4.422
 3.849
Dimethyl phthalate
 131-11-3
 13837329
 COC(=O)C1=CC=CC=C1C(=O)OC
 0.411
 -0.189
 -1.005
 -4.385
 3.940
Dimethyl succinate
 106-65-0
 13848341
 COC(=O)CCC(=O)OC
 0.337
 0.063
 -0.704
 -4.430
 3.830
N,N-Dimethyldecanamide
 14433-76-2
 24865
 CCCCCCCCCC(=O)N(C)C
 0.563
 -0.767
 -0.035
 -4.812
 4.103
Dimethyl isosorbide
 5306-85-4
 56694
 CO[C@@H]1CO[C@H]2[C@@H]1OC[C@@H]2OC
 0.353
 -0.132
 -0.394
 -4.083
 3.587
Dioctylsuccinate
 14491-66-8
 76204
 CCCCCCCCOC(=O)CCC(=O)OCCCCCCCC
 0.701
 -0.891
 -1.233
 -4.298
 3.966
1,3-Dioxolane
 646-06-0
 12066
 C1COCO1
 0.311
 -0.233
 -0.305
 -4.661
 4.029
Ethyl acetate
 141-78-6
 8525
 CCOC(=O)C
 0.262
 -0.298
 -0.700
 -4.868
 4.252
Ethyl laurate
 106-33-2
 7512
 CCCCCCCCCCCC(=O)OCC
 0.590
 -0.902
 -1.133
 -4.660
 4.124
Ethyl linoleate
 544-35-4
 4445379
 CCCCC/C=C\C/C=C\CCCCCCCC(=O)OCC
 0.531
 -0.837
 -1.094
 -4.519
 4.129
Ethyl linolenate
 1191-41-9
 4899352
 CC\/C=C\/C\/C=C\/C\/C=C\/CCCCCCCC(=O)OCC
 0.535
 -0.838
 -1.100
 -4.522
 4.135
Ethyl myristate
 124-06-1
 29023
 CCCCCCCCCCCCCC(=O)OCC
 0.601
 -0.934
 -1.168
 -4.585
 4.116
Geranyl acetate
 105-87-3
 1266019
 CC(=CCC\/C(=C\/COC(=O)C)\/C)C
 0.517
 -0.799
 -1.124
 -4.625
 4.128
Glycerol triacetate
 102-76-1
 13835706
 CC(=O)OCC(COC(=O)C)OC(=O)C
 0.325
 -0.139
 -0.913
 -4.381
 3.893
Glycerol-1,2,3-tributyl ether
 131570-29-1
 14757523
 CCCCOCC(COCCCC)OCCCC
 0.542
 -0.934
 -0.994
 -4.257
 4.082
Glycerol-1,2,3-triethyl ether
 162614-45-1
 477205
 CCOCC(COCC)OCC
 0.370
 -0.473
 -0.778
 -4.427
 4.078
Glycerol-1,2,3-trimethyl ether
 20637-49-4
 28056
 COCC(COC)OC
 0.315
 -0.358
 -0.407
 -4.280
 3.931
Glycerol-1,3-Dibutyl ether
 2216-77-5
 15806
 CCCCOCC(COCCCC)O
 0.423
 -0.658
 -0.583
 -3.592
 4.001
Isoamyle acetate
 123-92-2
 29016
 CC(C)CCOC(=O)C
 0.310
 -0.358
 -0.830
 -4.754
 4.262
Isobutyl acetate
 110-19-0
 7747
 CC(C)COC(=O)C
 0.251
 -0.237
 -0.798
 -4.771
 4.249
Isopropylacetate
 108-21-4
 7627
 CC(C)OC(=O)C
 0.232
 -0.186
 -0.803
 -4.708
 4.234
Isopropyl myristate
 110-27-0
 7751
 CCCCCCCCCCCCCC(=O)OC(C)C
 0.748
 -1.001
 -1.335
 -4.356
 4.041
Isosorbide dioctanoate
 64896-70-4
 8676465
 CCCCCCCC(=O)O[C@@H]1CO[C@H]2[C@@H]1OC[C@@H]2OC(=O)CCCCCCC
 0.618
 -0.827
 -1.092
 -4.216
 3.888
Methyl abietate
 127-25-3
 151113
 CC(C)C1=CC2=CC[C@@H]3[C@@]([C@H]2CC1)(CCC[C@@]3(C)C(=O)OC)C
 0.635
 -0.720
 -1.152
 -4.450
 4.083
Methyl acetate
 79-20-9
 6335
 CC(=O)OC
 0.217
 -0.055
 -0.657
 -4.563
 3.919
Methyl laurate
 111-82-0
 7847
 CCCCCCCCCCCC(=O)OC
 0.535
 -0.858
 -1.071
 -4.676
 4.090
Methyl linoleate
 112-63-0
 4447491
 CCCCC\/C=C\\C\/C=C\\CCCCCCCC(=O)OC
 0.505
 -0.806
 -1.028
 -4.524
 4.081
Methyl linolenate
 301-00-8
 4477947
 CC\/C=C\\C\/C=C\\C\/C=C\\CCCCCCCC(=O)OC
 0.510
 -0.794
 -1.023
 -4.523
 4.097
Methyl myristate
 124-10-7
 29024
 CCCCCCCCCCCCCC(=O)OC
 0.583
 -0.885
 -1.110
 -4.645
 4.078
Methyl oleate
 112-62-9
 4444205
 CCCCCCCC\/C=C\/CCCCCCCC(=O)OC
 0.572
 -0.852
 -1.072
 -4.523
 4.078
Glycerol-1-butyl monoether
 624-52-2
 62564
 CCCCOC(CO)CO
 0.452
 -0.493
 -0.285
 -3.531
 3.826
Dimethyl 2-methylglutarate
 14035-94-0
 105525
 CC(CCC(=O)OC)C(=O)OC
 0.344
 -0.144
 -0.783
 -4.365
 3.879
2-Methyltetrahydrofuran
 96-47-9
 7028
 CC1CCCO1
 0.344
 -0.557
 -0.565
 -4.686
 4.440
Menthanyl acetate
 247-546-8
 104829
 O=C(OC1(CCC(CC1)C(C)C)C)C
 0.568
 -0.685
 -1.121
 -4.472
 4.094
Menthyl acetate
 58985-18-5
 6379
 O=C(OC(C)(C)C1CCC(CC1)C)C
 0.566
 -0.697
 -1.117
 -4.508
 4.107
n-Propyl acetate
 109-60-4
 7706
 CCCOC(=O)C
 0.299
 -0.349
 -0.738
 -4.889
 4.267
Terpineol acetate
 8007-35-0
 99681
 CC1=CCC(CC1)C(C)(C)OC(=O)C
 0.470
 -0.618
 -1.089
 -4.541
 4.097
Tributyl citrate
 77-94-1
 6261
 CCCCOC(=O)CC(CC(=O)OCCCC)(C(=O)OCCCC)O
 0.572
 -0.723
 -0.887
 -3.892
 3.961
Triethyl citrate
 77-93-0
 13850879
 CCOC(=O)CC(CC(=O)OCC)(C(=O)OCC)O
 0.379
 -0.317
 -0.618
 -3.835
 3.826
Isopropyl alcohol
 67-63-0
 3644
 CC(C)O
 0.332
 -0.956
 0.341
 -3.781
 4.079
Dimethyl sulfoxide
 67-68-5
 659
 CS(=O)C
 0.304
 0.375
 0.599
 -4.534
 3.542
2-Furfuraldehyde
 98-01-1
 13863629
 C1=COC(=C1)C=O
 0.300
 0.023
 -0.539
 -4.305
 3.885
Propylene carbonate
 108-32-7
 7636
 CC1COC(=O)O1
 0.223
 0.302
 -1.030
 -4.388
 3.577
gamma-Valerolactone
 108-29-2
 7633
 CC1CCC(=O)O1
 0.293
 0.151
 -0.795
 -4.521
 3.957
Oleic acid
 112-80-1
 393217
 CCCCCCCC\/C=C\\CCCCCCCC(=O)O
 0.485
 -0.817
 -0.611
 -4.106
 4.042
Butyl myristate
 110-36-1
 7756
 CCCCCCCCCCCCCC(=O)OCCCC
 0.635
 -0.922
 -1.210
 -4.541
 4.108
Butyl palmitate
 111-06-8
 7799
 CCCCCCCCCCCCCCCC(=O)OCCCC
 0.623
 -0.917
 -1.210
 -4.541
 4.106
Butyl stearate
 123-95-5
 29018
 CCCCCCCCCCCCCCCCCC(=O)OCCCC
 0.615
 -0.917
 -1.208
 -4.538
 4.106
Cyclohexane
 110-82-7
 7787
 C1CCCCC1
 0.663
 -1.478
 -3.524
 -4.880
 4.653
p-Cymene
 99-87-6
 7183
 CC1=CC=C(C=C1)C(C)C
 0.564
 -1.163
 -3.112
 -4.797
 4.526
beta-Myrcene
 123-35-3
 28993
 CC(=CCCC(=C)C=C)C
 0.572
 -1.421
 -3.173
 -4.904
 4.599
Decamethylcyclo-pentasiloxane
 541-02-6
 10451
 C[Si]1(O[Si](O[Si](O[Si](O[Si](O1)(C)C)(C)C)(C)C)(C)C)C
 0.460
 -0.728
 -0.788
 -4.318
 3.963
Dipropyleneglycol
 110-98-5
 30467
 CC(CO)OCC(C)O
 0.392
 -0.442
 -0.225
 -3.468
 3.748
Ethyl oleate
 111-62-6
 4515636
 CCCCCCCC\/C=C\\CCCCCCCC(=O)OCC
 0.577
 -0.885
 -1.120
 -4.520
 4.114
Ethyl palmitate
 628-97-7
 11860
 CCCCCCCCCCCCCCCC(=O)OCC
 0.630
 -0.922
 -1.179
 -4.544
 4.111
Isopropyl palmitate
 142-91-6
 8567
 CCCCCCCCCCCCCCCC(=O)OC(C)C
 0.730
 -0.984
 -1.332
 -4.354
 4.040
d-Limonene
 5989-27-5
 389747
 CC1=CC[C@@H](CC1)C(=C)C
 0.558
 -1.298
 -3.188
 -4.832
 4.527
Methyl stearate
 112-61-8
 7909
 CCCCCCCCCCCCCCCCCC(=O)OC
 0.591
 -0.880
 -1.121
 -4.554
 4.074
Isododecane
 31807-55-3
 21934
 CCCCCCCCCC(C)C
 0.631
 -1.656
 -3.473
 -4.842
 4.548
Perfluorooctane
 307-34-6
 9018
 C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(C(C(C(F)(F)F)(F)F)(F)F)(F)F
 0.386
 -0.813
 -2.663
 -4.033
 4.079
alpha-Pinene
 80-56-8
 6402
 CC1=CCC2CC1C2(C)C
 0.544
 -1.225
 -3.200
 -4.719
 4.511
beta-Pinene
 127-91-3
 14198
 CC1(C2CCC(=C)C1C2)C
 0.543
 -1.245
 -3.217
 -4.723
 4.511
Terpinolene
 586-62-9
 10979
 CC1=CCC(=C(C)C)CC1
 0.544
 -1.209
 -3.212
 -4.860
 4.535
3-Methoxy-3-methyl-1-butanol
 56539-66-3
 55953
 CC(C)(CCO)OC
 0.310
 -0.637
 -0.200
 -3.916
 4.002
Benzyl alcohol
 100-51-6
 13860335
 C1=CC=C(C=C1)CO
 0.365
 -0.399
 -0.381
 -3.949
 4.143
1-Butanol
 71-36-3
 258
 CCCCO
 0.396
 -0.986
 0.145
 -3.914
 4.127
Cyclademol
 25225-09-6
 82475
 CC(C1CCCC(C1)(C)C)O
 0.463
 -1.076
 -0.413
 -4.012
 4.182
1-Decanol
 112-30-1
 7882
 CCCCCCCCCCO
 0.526
 -1.176
 -0.101
 -4.133
 4.188
Dihydromyrcenol
 18479-58-8
 27067
 CC(CCCC(C)(C)O)C=C
 0.479
 -1.150
 -0.458
 -4.025
 4.272
1,3-Dioxolane-4-methanol
 5660-53-7
 20317
 C1C(OCO1)CO
 0.404
 -0.250
 -0.108
 -3.641
 3.528
Ethanol
 64-17-5
 682
 CCO
 0.378
 -0.906
 0.337
 -3.574
 3.819
EthylHexyllactate
 6283-86-9
 83979
 CCCCC(CC)COC(=O)C(C)O
 0.515
 -0.690
 -0.821
 -3.643
 3.974
Ethyl lactate
 97-64-3
 13837423
 CCOC(=O)C(C)O
 0.242
 -0.026
 -0.412
 -3.575
 3.868
Geraniol
 106-24-1
 13849989
 CC(=CCC\/C(=C\/CO)\/C)C
 0.435
 -0.953
 -0.428
 -4.113
 4.238
Glycerol-1,3-diethyl ether
 4043-59-8
 70066
 CCOCC(COCC)O
 0.357
 -0.398
 -0.255
 -3.555
 3.864
Glycerol-1,2-dibutyl ether
 91337-36-9
 30991449
 CCCCOCC(CO)OCCCC
 0.437
 -0.680
 -0.624
 -3.709
 3.983
Glycerol-1,2-diethyl ether
 4756-20-1
 8139734
 CCOCC(CO)OCC
 0.361
 -0.415
 -0.244
 -3.663
 3.932
Glycerol-1,2-dimethyl ether
 40453-77-8
 10178881
 COCC(CO)OC
 0.338
 -0.410
 -0.121
 -3.525
 3.663
Glycerol-1,3-dimethyl ether
 623-69-8
 11690
 COCC(COC)O
 0.324
 -0.402
 -0.131
 -3.467
 3.676
Glycerol-1-ethyl monoether
 1874-62-0
 85025
 CCOCC(CO)O
 0.424
 -0.380
 -0.172
 -3.432
 3.583
Glycerol-2-butyl monoether
 100078-36-2
 62564
 OCC(OCCCC)CO
 0.452
 -0.493
 -0.285
 -3.531
 3.826
Glycerol-2-ethyl monoether
 22598-16-9
 14160289
 CCOC(CO)CO
 0.435
 -0.400
 -0.151
 -3.430
 3.579
Glycofurol (n=2)
 52814-38-7
 37039
 C1CC(OC1)COCCOCCO
 0.479
 -0.420
 -0.427
 -3.354
 3.673
N,N-Diethylolcapramide
 136-26-5
 55035
 CCCCCCCCCC(=O)N(CCO)CCO
 0.485
 -0.640
 -0.330
 -3.718
 3.857
Caprylic acid diethanolamide
 3077-30-3
 68969
 CCCCCCCC(=O)N(CCO)CCO
 0.476
 -0.532
 -0.279
 -3.717
 3.864
Isoamyl alcohol
 123-51-3
 29000
 CC(C)CCO
 0.349
 -1.101
 0.102
 -3.833
 4.283
Methyl ricinoleate
 141-24-2
 4510369
 CCCCCC[C@H](C\/C=C\\CCCCCCCC(=O)OC)O
 0.578
 -0.808
 -0.890
 -3.915
 3.979
Menthanol
 498-81-7
 9926
 OC(C)(C)C1CCC(C)CC1
 0.485
 -1.103
 -0.435
 -4.031
 4.184
Nopol
 128-50-7
 29138
 CC1(C2CC=C(C1C2)CCO)C
 0.365
 -0.784
 -0.385
 -4.026
 4.112
1-Octanol
 111-87-5
 932
 CCCCCCCCO
 0.461
 -1.066
 -0.057
 -4.141
 4.204
Oleyl alcohol
 143-28-2
 4447562
 CCCCCCCC\/C=C\\CCCCCCCCO
 0.361
 -1.033
 -0.386
 -4.081
 4.100
PolyEthyleneGlycol 600
 25322-68-3
 78633
 C(COCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO)O
 0.469
 -0.528
 -0.309
 -3.307
 3.502
Solketal
 100-79-8
 7247
 CC1(OCC(O1)CO)C
 0.297
 -0.208
 -0.251
 -3.678
 3.789
Ricinoleic acid
 141-22-0
 558800
 CCCCCC[C@H](C\/C=C\\CCCCCCCC(=O)O)O
 0.477
 -0.812
 -0.787
 -3.938
 3.971
alpha-Terpineol
 98-55-5
 13850142
 CC1=CCC(CC1)C(C)(C)O
 0.410
 -0.853
 -0.527
 -4.003
 4.172
beta-Terpineol
 138-87-4
 8418
 CC(=C)C1CCC(CC1)(C)O
 0.439
 -0.807
 -0.554
 -4.038
 4.158
Tetrahydrofurfurylic alcohol
 97-99-4
 7082
 C1CC(OC1)CO
 0.433
 -0.365
 -0.168
 -3.544
 3.857
1,3-Dioxan-5-ol
 4740-78-7
 70840
 C1C(COCO1)O
 0.407
 -0.238
 -0.110
 -3.616
 3.523
1,3-Dioxolane-4-methanol
 5464-28-8
 20317
 C1C(OCO1)CO
 0.404
 -0.250
 -0.108
 -3.641
 3.528
Ethylene glycol
 107-21-1
 13835235
 C(CO)O
 0.493
 -0.451
 0.375
 -2.968
 2.936
beta-Farnesen
 18794-84-8
 4476201
 CC(=CCC\/C(=C\\CCC(=C)C=C)\/C)C
 0.576
 -1.418
 -3.214
 -4.852
 4.470
Furfurylic alcohol
 98-00-0
 7083
 C1=COC(=C1)CO
 0.351
 -0.195
 -0.047
 -3.553
 3.880
Glycerol
 56-81-5
 733
 C(C(CO)O)O
 0.405
 -0.430
 0.076
 -3.421
 3.476
Glycerol carbonate
 931-40-8
 88417
 C1C(OC(=O)O1)CO
 0.282
 0.082
 -0.587
 -3.530
 3.529
Glycerol-1-methyl monoether
 623-39-2
 83791
 COCC(CO)O
 0.394
 -0.376
 -0.106
 -3.403
 3.510
Glycerol-2-methyl monoether
 761-06-8
 9346023
 COC(CO)CO
 0.403
 -0.429
 -0.108
 -3.382
 3.500
5-(Hydroxymethyl)furfural
 67-47-0
 207215
 C1=C(OC(=C1)C=O)CO
 0.413
 0.084
 -0.314
 -3.451
 3.729
3-Hydroxypropionic acid
 503-66-2
 61460
 C(CO)C(=O)O
 0.324
 -0.155
 -0.180
 -3.758
 3.500
PolyEthyleneGlycol 200
 112-60-7
 7908
 C(COCCOCCOCCO)O
 0.490
 -0.423
 -0.310
 -3.297
 3.495
1,3-Propanediol
 504-63-2
 13839553
 C(CO)CO
 0.434
 -0.627
 0.236
 -3.726
 3.600
propylene glycol
 57-55-6
 13835224
 CC(CO)O
 0.387
 -0.447
 0.259
 -3.447
 3.586
Acetic acid
 64-19-7
 171
 CC(=O)O
 0.193
 0.016
 -0.103
 -3.625
 3.565
Propionic acid
 79-09-4
 1005
 CCC(=O)O
 0.207
 -0.105
 -0.185
 -3.981
 3.840
Water
 7732-18-5
 937
 O
 0.305
 -0.832
 -1.252
 -3.528
 3.762

Chemical Space

To explore the chemical space, each coefficient was multiplied by the average values for solute coefficients (E=0.884, S=0.996, A=0.174, B=0.487, V=1.299) from ADModel003. Then PCA was computed for (eE, sS, aA, bB, vV) using the following code:
setwd("C:/Dropbox/research/AbrahamSolventCoefficients/MakingCZero/SustainableSolvents")
mydata = read.csv(file="SustainableSolventsPaperCompletePCA.csv",head=TRUE,row.names="Title")
pc1 <- prcomp(mydata, scale. = T)
x <- pc1$x
summary(pc1)
 
[output]
Importance of components:
                          PC1    PC2    PC3     PC4     PC5
Standard deviation     1.6844 1.0788 0.7738 0.55322 0.30719
Proportion of Variance 0.5674 0.2328 0.1197 0.06121 0.01887
Cumulative Proportion  0.5674 0.8002 0.9199 0.98113 1.00000
[output]
 
write.csv(x, file = "PCA.csv")
The following image was generated using Tableau Public v8.2. Solvents with known (measured) coefficients are squares and solvents with ony predicted coefficients are circles. Green solvents are coloured green.

Lots of the green solvents around methyl palmitate seem to occupy a new region of the chemical space not covered by current solvents with measured coefficients. Similarly ethyl lactate and acetic acid seem to be possibly useful novel solvents with different solvation properties than those with measured coefficients. On the other hand, there are not many green solvent alternatives for classical solvents around p-xylene.

Alternative Solvents

We can use chemical space information to make general green solvent recommendations (as is done with GSK and others). For example the predicted solvent coefficients for propylene glycol (green) are 'close' to the experimental values for methanol.

propylene glycol
 57-55-6
 13835224
 CC(CO)O
 0.387
 -0.447
 0.259
 -3.447
 3.586
methanol
 67-56-1
 864
 CO
 0.286
 -0.631
 0.312
 -3.417
 3.572

This suggests that propylene glycol can used as a general substitute for methanol. To examine this we compare the solubility values of compounds that have values in both solvents. We do not expect to see exact agreement (as the coefficients are firstly predicted and secondly not identical) but we do see that solubility values are of the same order in most cases. The biggest discrepancy being for dimethyl fumerate. The measured solubility values are reported to be 0.182 M and 0.005 M for methanol and propylene glycol respectively. This is not something one would necessarily expect and the reported value or values may be incorrect. Substituting propylene glycol for methanol is just one of many recommendations that can be made using this technique.

Similarly, by measuring the difference between two solvent logP values (and using the compound-specific solute descriptors E,S,A,B,V) as follows:

d = logP_1 - logP_2 = logS_1 - logS_2 = (e_01-e_02)*E + (e_01-e_02)*S + (e_01-e_02)*A + (e_01-e_02)B + (e_01-e_02)*V

we get a good idea of pairs of solvents with similar solvation properties for specific individual compounds (the closer to zero, the better). By comparing classical (non-green) solvents with all green solvents, we can make recommended green solvent replacements for non-green solvents. As an example, we calculate recommended green solvent replacements for benzoic acid, see table below, using descriptors E=0.730, S=0.90, A=0.59, B=0.40, V=0.9317 (using d=0.01).[3] The recommendations make sense in general and several examples can be explicitly verified by comparing actual measured solubility values.[4]. Such a procedure can easily be done for other specific compounds with known or predicted Abraham descriptors to find alternative green solvents in varying specific circumstances (solubility, partition, etc). Note the solvents at the bottom with no green alternatives.
classic solvent
 green
 green
 green
 green
 green
1-propanol
 Glycerol-1-ethyl monoether
 Glycerol-2-ethyl monoether
 1,3-Dioxolane-4-methanol
 glycerol
 Cyclopentyl methyl ether
 Glycerol-1,3-dimethyl ether
 2-Furfuraldehyde
acetylacetone
 Glycerol-1-ethyl monoether
 Glycerol-2-ethyl monoether
 Caprylic acid diethanolamide
 glycerol
 Cyclopentyl methyl ether
 Glycerol-1,3-dimethyl ether
 2-Furfuraldehyde
3-methyl-2-butanone
 3-methyl-1-butanol
 Glycerol-1-ethyl monoether
 Glycerol-2-ethyl monoether
 Caprylic acid diethanolamide
 glycerol
 Cyclopentyl methyl ether
 2-Furfuraldehyde
2-methyl-2-propanol
 3-methyl-1-butanol
 Glycerol-1-ethyl monoether
 Glycerol-2-ethyl monoether
 Caprylic acid diethanolamide
 glycerol
 Cyclopentyl methyl ether
 2-Furfuraldehyde
triethylene glycol
 Glycerol-1-ethyl monoether
 Glycerol-2-ethyl monoether
 1,3-Dioxolane-4-methanol
 glycerol
 Cyclopentyl methyl ether
 Glycerol-1,3-dimethyl ether
diethylene glycol
 Glycerol-1-ethyl monoether
 Glycerol-2-ethyl monoether
 1,3-Dioxolane-4-methanol
 glycerol
 Cyclopentyl methyl ether
 Glycerol-1,3-dimethyl ether
nitroethane
 Ethyl laurate
 Dibutyl sebacate
 Butyl myristate
 Butyl palmitate
 Methyl laurate
 Butyl stearate
methanol
 ethanol
 Solketal
 Glycerol-1,3-diethyl ether
 Glycerol-1,2-diethyl ether
 Propionic acid
cyclohexanone
 gamma-Valerolactone
 N,N-Dimethyloctanamide
 3-Hydroxypropionic acid
 trimethylene glycol
 Glycerol-2-methyl monoether
3-pentanol
 gamma-Valerolactone
 N,N-Dimethyloctanamide
 3-Hydroxypropionic acid
 trimethylene glycol
 Glycerol-2-methyl monoether
4-picoline
 ethanol/water(80:20)vol
 Glycerol-1,2-dimethyl ether
 Glycofurol (n=2)
 Glycerol-1-methyl monoether
 Glycerol carbonate
acetophenone
 1-octanol
 ethyl acetate
 Glycerol-1,2,3-trimethyl ether
 PolyEthyleneGlycol 600
 Dimethyl isosorbide
2-methyl-2-butanol
 3-methyl-1-butanol
 Caprylic acid diethanolamide
 glycerol
 Cyclopentyl methyl ether
 2-Furfuraldehyde
DEGDME
 butyl acetate
 ethanol/water(60:40)vol
 n-Propyl acetate
 Isoamyle acetate
pyridine
 gamma-Valerolactone
 N,N-Dimethyloctanamide
 trimethylene glycol
 Glycerol-2-methyl monoether
2-pentanol
 gamma-Valerolactone
 N,N-Dimethyloctanamide
 trimethylene glycol
 Glycerol-2-methyl monoether
4-methyl-2-pentanone
 1-decanol
 Isobutyl acetate
 Nopol
 Glycerol-1,2-dibutyl ether
pyrrolidine
 Geraniol
 beta-Terpineol
 Dimethyl 2-methylglutarate
 EthylHexyllactate
2,6-dimethylpyridine
 1-octanol
 ethyl acetate
 Glycerol-1,2,3-trimethyl ether
 Dimethyl isosorbide
trifluoroethanol
 Methyl ricinoleate
 1,4-Cineol
 Diethyl phthalate
 Diisobutyl succinate
ethyl formate
 Methyl ricinoleate
 1,4-Cineol
 Diethyl phthalate
 Diisobutyl succinate
sulfolane
 ethylene glycol
 ethanol/water(70:30)vol
 Glycerol-1,3-Dibutyl ether
 2-Methyltetrahydrofuran
1-hexanol
 Dimethyl succinate
 N,N-Diethylolcapramide
 3-Methoxy-3-methyl-1-butanol
 2-Methyltetrahydrofuran
piperidine
 Oleic acid
 Menthanol
 Tributyl citrate
formamide
 1-decanol
 Isobutyl acetate
 Nopol
DEGDEE
 1-decanol
 Isobutyl acetate
 Nopol
3,3-dimethyl-2-butanone
 1-octanol
 ethyl acetate
 N,N-Dimethyldecanamide
ethyl benzoate
 Diethyl adipate
 Diethyl phthalate
 Diisobutyl succinate
dibenzyl ether
 Diethyl adipate
 Diethyl phthalate
 Diisobutyl succinate
propionitrile
 Methyl ricinoleate
 1,4-Cineol
 Diisobutyl succinate
benzonitrile
 Methyl ricinoleate
 1,4-Cineol
 Diisobutyl succinate
diethylamine
 Glycerol-1,2,3-triethyl ether
 Dihydromyrcenol
 Cyclademol
di-n-propyl ether
 Glycerol-1,2,3-triethyl ether
 Dihydromyrcenol
 Cyclademol
quinoline
 ethanol/water(60:40)vol
 Geraniol
 alpha-Terpineol
diethyl ether
 Geraniol
 EthylHexyllactate
 alpha-Terpineol
1-pentanol
 1-butanol
 PolyEthyleneGlycol 200
 1,3-Dioxolane
2,4-dimethylpyridine
 Glycerol-1,3-Dibutyl ether
 Triethyl citrate
pentyl actetae
 Oleic acid
 Tributyl citrate
TEGDME
 propylene carbonate
 octadecanol
2,4-dimethyl-3-pentanone
 ethyl acetate
 N,N-Dimethyldecanamide
diphenyl ether
 Butyl laurate
 Isopropyl palmitate
acetic anhydride
 ethylene glycol
 Glycerol-1,3-Dibutyl ether
2-methyl-1-propanol
 ethylene glycol
 Glycerol-1,3-Dibutyl ether
3-pentanone
 methyl acetate
 Glycerol-1,2-dibutyl ether
2-aminoethanol
 Glycofurol (n=2)
 Glycerol-1-methyl monoether
methyl formate
 Glycerol triacetate
 Dimethyl phthalate
aniline
 Glycerol triacetate
 Dimethyl phthalate
2,4,6-trimethylpyridine
 Glycerol triacetate
 Dimethyl phthalate
phenetole
 Decamethylcyclo-pentasiloxane
 Diisoamylsuccinate
methyl tert-butyl ether
 Dimethyl glutarate
 Diethyl succinate
methyl benzoate
 1,8-Cineol
 Diethyl glutarate
diethyl carbonate
 1,8-Cineol
 Diethyl glutarate
anisole
 1,8-Cineol
 Diethyl glutarate
1,2-dimethoxyethane
 ethanol/water(60:40)vol
 alpha-Terpineol
N-formylmorpholine
 benzyl alcohol
 acetic acid
2,6-dimethyl-4-heptanone
 Methyl ricinoleate
 1,4-Cineol
di-isopropyl ether
 Triethyl citrate
1-heptanol
 Triethyl citrate
nitromethane
 Ricinoleic acid
n-propylamine
 Ricinoleic acid
carbon disulfide
 p-Cymene
propyl formate
 Menthanol
phenol
 Menthanol
1,1-dichloroethane
 isopropyl myristate
undecane
 Isododecane
nonane
 Isododecane
heptane
 Isododecane
ethyl propionate
 Isobutyl acetate
3-picoline
 Glycerol-1-methyl monoether
morpholine
 ethanol/water(90:10)vol
toluene
 ethanol/water(20:80)vol
tetrachloroethylene
 ethanol/water(20:80)vol
bromobenzene
 ethanol/water(20:80)vol
triethylamine
 Diisobutyl adipate
ethylenediamine
 Diisobutyl adipate
1,9-decadiene
 beta-Myrcene
cyclohexanol
 acetone
butanone
 acetone
2-butanol
 acetone
N,N-dimethylaniline
 1,8-Cineol
butyronitrile
 1,4-Cineol
Z-1,2-dichloroethylene
trifluoroacetic acid
trichloroethylene
tributylamine
tributyl phosphate
THF
styrene
pentane
p-xylene
octane
o-xylene
o-dichlorobenzene
nitrobenzene
N,N-dimethylacetamide
N-methylpyrrolidinone
N-methylformamide
N-methylacetamide
N-methyl-2-piperidone
N-ethylformamide
N-ethylacetamide
n-butylamine
methylcyclohexane
mesitylene
m-xylene
m-dichlorobenzene
m-cresol
iodoethane
iodobenzene
HMPTA
hexane
hexadecane
fluorobenzene
ethylbenzene
DPMU
dodecane
DMF
DMEU
dimethylacetamide
diethylacetamide
dichloromethane
dibutylformamide
dibutyl ether
decane
cyclopentanone
cyclopentane
cyclohexene
cis-decaline
chloroform
chlorobenzene
carbon tetrachloride
bromoethane
benzene
benzaldehyde
acetonitrile
2,2,4-trimethylpentane
2-pentanone
2-methoxyethanol
2-chloropropane
1,4-dioxane
1,2-dichloroethane
1,1,3,3-tetramethyl urea
1,1,2,2-tetrachloroethane
1,1,1-trichloroethane
1,1-dichloroethylene
1-hexadecene
1-chloropropane
1-chlorobutane
1-bromobutane

Conclusion

Models for Abraham solvent coefficients were used to produce predictions for 203 solvents with unknown solvent coefficients, 118 of which are "sustainable solvents." We then presented two techniques whereby sustainable solvents could be chosen as possible replacements for non-green solvents. First, generally, by proximity (and classification) within a chemical space created by principal component analysis; and second, specfically, for compounds with known (or predicted) Abraham coefficients. Benzoic acid was used as an example and predictions matched well with measurements.

References

[1] Laurianne Moity, Morgan Durand, Adrien Benazzouz, Christel Pierlot, Valérie Moliniera, and Jean-Marie Aubry. Panorama of sustainable solvents using the COSMO-RS approach. Green Chem., 2012,14, 1132-1145, doi: 10.1039/C2GC16515E
[2] Paul C.M. van Noort. Solvation thermodynamics and the physical–chemical meaning of the constant in Abraham solvation equations. Chemosphere (2011), doi:10.1016/j.chemosphere.2011.11.073
[3] Michael H. Abraham and William E. Acree Jr. The solubility of liquid and solid compounds in dry octan-1-ol. Chemosphere, Volume 103, May 2014, Pages 26–34. doi: 10.1016/j.chemosphere.2013.10.095
[4] Solubility of benzoic acid in organic solvents .